4-Toluenesulfonyl chloride → HCID 19967235, compound

HRID 976441Notes

Reaction equation

HRID 976441 reaction equation
[OH:1][CH2:2][C:3]1([CH2:18][OH:19])[CH2:17][CH:6]2[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][CH:5]2[CH2:4]1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[CH3:30][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:1][CH2:2][C:3]2([CH2:18][O:19][S:26]([C:23]3[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=3)(=[O:28])=[O:27])[CH2:17][CH:6]3[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:9][CH:5]3[CH2:4]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 19967234HCID 19967234, compound

Product 1

HCID 19967235HCID 19967235, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The diol compound prepared in Example K is dissolved in pyridine and treated with p-toluenesulfonyl chloride at -10° C., warmed to room temperature over two hours, diluted with aqueous sodium bicarbonate and extracted into chloroform to afford the title compound in 93% yield. This material is used without further purification. 1HNMR (400 MHz, CDCl3): β=1.26 ppm (m, 2H); 1.45 (s, 9H); 1.80 (m, 2H); 2.47 (s, 6H); 2.59 (m, 2H); 3.10 (d, 2H); 3.39 (dd, 2H); 3.78 (s, 2H); 3.85 (s, 2H); 7.36 (m, 4H); 7.72 (m, 4H).

Workup

  1. extractionextracted into chloroform

Sources & evidence

ORD record
ord-daed0ffc3d2a44bfb7eaf2a59eef323f
Source dataset
uspto-grants-1997_03
Patent number
US05612366

Reaction notes

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